Potassium Fluoride → HCID 18922547, compound

Participants

Reaction Steps

A mixture of 1-(2-quinolinyl)-3-trifluoromethyl-5-hydroxypyrazole (533 mg; 1.91 mmol) and KF (220 mg; 3.8 mmol) in 35 ml of DMF was stirred under nitrogen at room temperature for 10 minutes and then 2-bromomethyl-4-isopropyl-6-methoxy-1,2-benzisothiazol-3(2H)-one 1,1-dioxide (592 mg, 1.7 mmol) was added. The reaction mixture was stirred at room temperature for 45 minutes and diluted with ice/cold saturated sodium bicarbonate solution. The mixture was extracted with ethyl acetate (3×) followed by the addition of ether, the organic layer was washed with water, dried over magnesium sulfate, and concentrated in vacuo. The residue was triturated with ethyl acetate/ether to yield a white solid, which was crystallized (from hot ethyl acetate/ether followed by methylene chloride/ether) and dried to afford 710 mg (76%) of 4-isopropyl-6-methoxy-2-[1-(2-quinolinyl)-3-(trifluoromethyl)pyrazol-5-yl-oxymethyl]-1,2-benzisothiazol-3(2H)-one 1,1-dioxide (Formula I: R1 =2-quinolinyl; R2 =CF3 ; R3 =H; R4 =CH(CH3)2 ; R5 =6-OCH3) as a white solid, m.p. 124°-125° C.

Provenance & Evidence